Dimethylformamide → HCID 23369721, compound

HRID 1900779Notes

Reaction equation

HRID 1900779 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[NH:8][C:7](=[O:13])[CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].[CH2:20](I)[CH:21]=[CH2:22].CN(C)C=O>C(Cl)(Cl)Cl>[CH2:22]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[NH:8][C:7](=[O:13])[CH:6]=[CH:5]2)[CH:21]=[CH2:20]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11166Allyl iodideHCID 11430Potassium CarbonateHCID 10464809HCID 10464809, compound

Product 1

HCID 23369721HCID 23369721, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 6-hydroxy-8-methylcarbostyril (15.0 g, 85.7 mmol), potassium carbonate (23.4 g, 169.5 mmol), allyl iodide (15.6 g, 90.0 mmol), and N,N-dimethylformamide (120 ml) was stirred in a bath of 70° C. for 1.5 hours. The mixture was condensed, and the residue was dissolved in chloroform, followed by washing with water and 2N-NaOH. The washed material was dried and condensed. The resultant residue was recrystallized (chloroform--n-hexane) to obtain 10.11 g of 6-allyloxy-8-methylcarbostyril as pale brown prisms (54.8%).

Workup

  1. customcondensed
  2. washby washing with water and 2N-NaOH
  3. customThe washed material was dried
  4. customcondensed
  5. customThe resultant residue was recrystallized (chloroform--n-hexane)

Sources & evidence

ORD record
ord-5cb97bb1796c4dd4b0a17e4f4a0a047c
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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